Winchester County VA Homes for Sale

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  /11

  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
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  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout.Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  601 Gray Ave, Winchester, VA 22601
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  /43

  $350,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,230 Sq Ft

  117 E Pall Mall St, Winchester, VA 22601

  ** Price improvement!** Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump

  

  Becky Wallace

  Pearson Smith Realty, LLC

  117 E Pall Mall St, Winchester, VA 22601
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  /9

  $689,000

  $611K PRICE DROP

  • Land
  • 64.91 Acres
  • $10,615 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  The seller has made a significant price adjustment to better align the property with current market conditions, creating an outstanding opportunity for buyers. With the new pricing, this property offers exceptional value and is positioned for serious consideration. If you've previously considered this property, now is the time to take another look. Rare opportunity to own 64+ scenic acres on the

  

  Lori Bales

  Keller Williams Realty

  Lot 7 Cedar Creek Grade, Winchester, VA
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  /3

  $339,000

  $11K PRICE DROP

  • Studio
  • 1,654 Sq Ft

  211, 213-215 E Clifford St, Winchester, VA 22601

  Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath.The properties are deeded

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  211, 213-215 E Clifford St, Winchester, VA 22601
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  /41

  $500,900

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  609 Quartzite Cir, Winchester, VA 22601

  Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides

  

  Walther Vasquez Johnson

  Samson Properties

  609 Quartzite Cir, Winchester, VA 22601
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  /2

  $175,000

  • Land
  • 16,117 Sq Ft
  • $472,973 per Acre

  719 Kennedy Dr, Winchester, VA 22601

  Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

  

  Frank Armstrong, IV

  Colony Realty

  719 Kennedy Dr, Winchester, VA 22601
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  /51

  $499,900

  • 3 Beds
  • 3 Baths
  • 1,564 Sq Ft

  510 S Cameron St, Winchester, VA 22601

  Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special.Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to

  

  Brock Harris

  Samson Properties

  510 S Cameron St, Winchester, VA 22601
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  /40

  $350,000

  $20K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,588 Sq Ft

  1008 S Cameron St, Winchester, VA 22601

  Live just minutes from historic Old Town Winchester, where charming boutiques, local restaurants, and picturesque streets are all close at hand. This beautifully maintained two-story home seamlessly blends the timeless character of the 1930s with the modern updates today’s buyers appreciate.A classic covered front porch welcomes you home and offers the perfect place to enjoy your morning

  Nikola Tadie Redfin Corporation

  1008 S Cameron St, Winchester, VA 22601
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  /52

  $839,000

  • 4 Beds
  • 4.5 Baths
  • 4,697 Sq Ft

  922 Armistead St, Winchester, VA 22601

  Welcome to 922 Armistead Street, a spacious brick Colonial in Winchester's established Morlyn Hills neighborhood offering approximately 4,697 finished square feet across three levels. The light-filled main level features hardwood floors, a private office with built-ins, formal living and dining rooms, and a generous kitchen with island and breakfast area opening to the family room with fireplace.

  Debbie Crevier Kent Cottage Street Realty LLC

  922 Armistead St, Winchester, VA 22601
• 

  

  /19

  $329,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,576 Sq Ft

  Juniper Plan at Old Town Green, Winchester, VA 22601

  Welcome to Ryan Homes at Old Town Green, experience life in Old Town Winchester with the city's lowest priced garage townhomes, just a short walk to shops, dining and recreation.The Juniper townhome combines all the amenities of single-family living with total convenience. The main level is highlighted by a gourmet kitchen that's open to the living area so you'll never miss a moment. The

  Ryan Homes Builder

  306 Smalts Cir Unit 41303475, Winchester, VA 22601
• 

  

  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

  Chad Pangle Whitetail Properties Real Estate

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
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  /29

  $369,999

  • 3 Beds
  • 2 Baths
  • 1,387 Sq Ft

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  Home Warranty for the Buyer + Bonus for the Buyer’s Agent with a Ratified Contract in September! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom

  Patricia Rivas Plata Keller Williams Realty Dulles

  2919 S Pleasant Valley Rd, Winchester, VA 22601
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  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /19

  $395,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  648 Arden Ct, Winchester, VA 22601

  648 Arden Court is an attractive new 3 level townhome backing to trees with brick in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, grey cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  648 Arden Ct, Winchester, VA 22601
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  /37

  $400,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,431 Sq Ft

  1826 Kershaw Ln, Winchester, VA 22601

  Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester.This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open

  RoxAnn Grimes RE/MAX Roots

  1826 Kershaw Ln, Winchester, VA 22601
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  /63

  $480,000

  $109K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  832 Winder Ct, Winchester, VA 22601

  Listed below recent appraised value.All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining.Recent interior updates include new hardwood flooring in the main living room,

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
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  /103

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 3,497 Sq Ft

  466 Merrimans Ln, Winchester, VA 22601

  Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom.The finished lower level provides outstanding

  John Schroth Colony Realty

  466 Merrimans Ln, Winchester, VA 22601
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  /5

  $295,000

  Coming Soon Oct 30

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality.The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
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  /30

  $400,000

  • 3 Beds
  • 2.5 Baths
  • 2,330 Sq Ft

  3135 Eton Place, Winchester, VA 22601

  Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing stores, and professional services allows you to start or end your day at a plethora of local store fronts only steps from your home. Being only 2 years young allows the comfort of practically a new home in impeccable condition. Two car

  Dave Spence RE/MAX Roots

  3135 Eton Place, Winchester, VA 22601
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  /36

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,493 Sq Ft

  501 Fox Dr, Winchester, VA 22601

  Welcome to this beautifully updated 4 bedroom, 2 full bath home in the heart of Winchester City! This move in-ready property offers fresh paint throughout, newly installed laminate flooring, new carpet in the bedrooms and new ceiling fans, and a fully finished basement providing additional living space. The kitchen features a new dishwasher, while recent updates include a new dryer, toilet, and

  Jacob Schuttinger Coldwell Banker Premier

  501 Fox Dr, Winchester, VA 22601
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  /39

  $425,000

  $9K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  422 S Loudoun St, Winchester, VA 22601

  PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen,

  Dana Cloud Realty ONE Group Old Towne

  422 S Loudoun St, Winchester, VA 22601
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  /46

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,592 Sq Ft

  805 S Kent St, Winchester, VA 22601

  Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or

  Carolina Mosquera Weichert, REALTORS

  805 S Kent St, Winchester, VA 22601
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  /9

  $308,000

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  2519 Hockman Ave, Winchester, VA 22601

  This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full

  Meridee Powars Link Realty Services LLC

  2519 Hockman Ave, Winchester, VA 22601
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  /44

  $299,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  12 N Purcell Ave, Winchester, VA 22601

  Welcome to 12 N Purcell Ave, a classic white bungalow offering standout curb appeal, a well-kept lawn and landscaping, and an unbeatable central location. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor

  Dan Whitacre Colony Realty

  12 N Purcell Ave, Winchester, VA 22601
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  /63

  $699,000

  • 7 Beds
  • 5 Baths
  • 4,736 Sq Ft

  2700 Loyalty Ct, Winchester, VA 22601

  Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a

  Dan Whitacre Colony Realty

  2700 Loyalty Ct, Winchester, VA 22601
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  /30

  $409,000

  • 4 Beds
  • 1 Bath
  • 1,768 Sq Ft

  322 E Piccadilly St, Winchester, VA 22601

  Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening

  LESLIE WEBB Long & Foster Real Estate, Inc.

  322 E Piccadilly St, Winchester, VA 22601
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  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
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  /29

  $357,500

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  621 Patterson Ave, Winchester, VA 22601

  Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort.The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel

  LESLIE WEBB Long & Foster Real Estate, Inc.

  621 Patterson Ave, Winchester, VA 22601
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  /3

  $429,900

  Coming Soon Oct 15

  • 5 Beds
  • 2 Baths
  • 1,971 Sq Ft

  337 George St, Winchester, VA 22601

  Fantastic location, classic brick charm, and plenty of space! This well-located brick rambler offers easy access to Route 50, Route 37, and I-81, while being just minutes from Valley Health. A long driveway, carport, concrete patio, and large, level backyard provide plenty of outdoor space and convenience.Inside, you’re welcomed by a light and bright living room featuring beautiful hardwood

  Heloisa Amar Samson Properties

  337 George St, Winchester, VA 22601
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  /33

  $300,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /127

  $3,175,000

  • 6 Beds
  • 7 Baths
  • 8,593 Sq Ft

  730 Merrimans Ln, Winchester, VA 22601

  A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern LuxuryRarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century

  Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

  730 Merrimans Ln, Winchester, VA 22601
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  /52

  $530,000

  • 5 Beds
  • 3.5 Baths
  • 2,417 Sq Ft

  1605 Fort Braddock Ct, Winchester, VA 22601

  Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus

  Timothy Kotlowski Long & Foster Real Estate, Inc.

  1605 Fort Braddock Ct, Winchester, VA 22601
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  /26

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  2817 Papermill Rd, Winchester, VA 22601

  Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent

  Kevin Rodriguez Weichert, REALTORS

  2817 Papermill Rd, Winchester, VA 22601
• 

  

  /96

  $449,999

  $40K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
• 

  

  /17

  $396,190

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  660 Arden Ct, Winchester, VA 22601

  660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  660 Arden Ct, Winchester, VA 22601
• 

  

  /38

  $529,000

  • Studio
  • 3,688 Sq Ft

  440 N Braddock St, Winchester, VA 22601

  An exceptional multifamily investment opportunity awaits in the heart of historic downtown Winchester! Located at 440 N Braddock St, this turnkey property features a timeless brick exterior, rich historic charm, and beautiful hardwood floors throughout. The property comprises three distinct, light-filled units, each designed with two spacious bedrooms and one full bathroom. Tenants will love the

  Dan Whitacre Colony Realty

  440 N Braddock St, Winchester, VA 22601
• 

  

  /71

  $735,000

  • 3 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  1748 Handley Ave, Winchester, VA 22601

  Exceptional space, thoughtful updates, and tremendous future potential come together in this impressive home! With a brand-new HVAC system, freshly painted interior and exterior, a freshly painted deck, and beautifully refreshed hardwood floors in the living room, much of the work has already been done for the next owner. Seller has obtained a recent professional appraisal; contact listing agent

  Barbara Smith RE/MAX Real Estate Connections

  1748 Handley Ave, Winchester, VA 22601
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601

Showing Results 1 - 40, Page 1 of 3